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Full text of "Practical Organic Chemistry"

I

PHENYLHYDRAZINE                           173
The base, which has a brown colour, is filtered and dissolved
in hot spirit, with the addition of a few drops of concentrated                      «
ammonia.    Yield, about 8 grams.
C0H6N:N.NHC0H6 + H.C0H4NH2.HC1 -
C0H5N:N.C0H4.NH2 + CCH5NH2.HC1.                        I
Properties.—Orange prisms ; m. p. 127°.                                                       , J
Reaction.—Make a solution of 4 grams stannous chloride in
10 c.c. cone, hydrochloric acid, add 2 grams aminoazobenzene,                       J»'
and boil for a few minutes.    On cooling crystals of the hydro-                      /
chlorides  of   aniline   and  ^-phenylenediamine  separate   out.                      1
The  liquid  is filtered  and  washed with a little cone, hydro-                      ;" j,
chloric  acid  to  remove  the  tin salts.     If the   precipitate   is                       ' \>
dissolved  in  water  and   made alkaline with  caustic soda, a                       '*
mixture of liquid aniline and solid/-phenylenediamine is pre-                       \
cipitated, from which the former may be removed by filtering,
washing, and draining on a porous plate.                                                          ^;
C0HBN:N.C0H4NHo + "2SnCl2 + 4HC1=                                                          />
C0H5NH2 4- H2N.CGH4.NH2 + 2SnCl4.                           '*
/-Phenylenediamine, when warmed with dilute sulphuric acid                        ''
and potassium bichromate or lead peroxide, gives the odour of                        ji
quinone (p.-192).    After warming and cooling, extract with ether.                       flL
The ethereal solution has a yellow colour.    Decant the ether                       1p
extract on to a watch-glass and leave it to evaporate in the air.                       'ft
A deposit of microscopic yellow crystals remains.    See Appen-                      * ,,
diX) p. 286.                                                                                                        ||*
**\
PREPARATION  71.                                                   ^
Phenylhydrazine, C0H5NH,NH2                                        -,f
E.  Fischer, Annalen,   1878, 190, .167 ; Meyer, Lecco,   Ber^                      \\. '
1883, 16, 2976 ; Meyer and Jacobson, Lchrlntch, 2, 305.                           ^
20 grms. aniline.                                                                                !\ ^
200 „ (170 c.c.) cone, hydrochloric acid.                                         ' *
20 „ sodium nitrite (in 100 c.c. water).                                        ^
120 „ crystallised stannous chloride (in  100 c.c. ^
cone, hydrochloric acid). .                                           ?;'
1 |f*
The  aniline is dissolved  in  the  concentrated hydrochloric                       k\(
acid and cooled to o° in a freezing mixture.    The solution of                     ' i (.